Ethyl Acetate → HCID 73853384, compound

HRID 1245012Notes

Reaction equation

HRID 1245012 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH:19]=[CH:20][CH2:21][OH:22])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(OCC)(=O)C>CS(C)=O.[O-2].[Mn+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][CH:10]=[C:11]([CH:19]=[CH:20][CH:21]=[O:22])[C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69589156HCID 69589156, compound

Product 1

HCID 73853384HCID 73853384, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

16.32 g of activated manganese oxide were added to a solution of 1.63 g (5.54 mmol) of 2-(4-fluorophenyl)-4-(3-hydroxy-1-propen-1-yl)-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in step 66(i) above] in 80 ml of dimethylsulfoxide. The resulting mixture was stirred at room temperature for 24 hours. At the end of this time, ethyl acetate was added to the reaction mixture and then this was filtered. Water was added to the resulting filtrate and then this was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure. The residue thus obtained was washed with dichloromethane to afford 1.36 g (yield 84%) of the title compound as a pale brown powder.

Workup

  1. filtrationthis was filtered
  2. additionWater was added to the resulting filtrate
  3. extractionthis was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue thus obtained
  9. washwas washed with dichloromethane

Sources & evidence

ORD record
ord-2b95648dc8524b33a078538e6177ff6d
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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